7,8,9,10-Tetrahydrobenzo[a]pyren-7-ol is a benzopyrene analogue that is activated by liver cytosol to form an electrophilic sulfate ester capable of forming covalent DNA adducts and inducing mutations.

Physicochemical Properties

Molecular Formula	C20H16O
Molecular Weight	272.34
Exact Mass	272.12
CAS #	6272-55-5
PubChem CID	97714
Appearance	Light brown to brown solid powder
Density	1.3±0.1 g/cm3
Boiling Point	508.5±19.0 °C at 760 mmHg
Melting Point	142-144ºC(lit.)
Flash Point	189.2±13.7 °C
Vapour Pressure	0.0±1.4 mmHg at 25°C
Index of Refraction	1.836
LogP	5.01
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	0
Heavy Atom Count	21
Complexity	405
Defined Atom Stereocenter Count	0
InChi Key	VKUQFYXBPGXTKI-UHFFFAOYSA-N
InChi Code	InChI=1S/C20H16O/c21-18-6-2-5-15-16-10-9-13-4-1-3-12-7-8-14(11-17(15)18)20(16)19(12)13/h1,3-4,7-11,18,21H,2,5-6H2
Chemical Name	7,8,9,10-tetrahydrobenzo[a]pyren-7-ol
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ADME/Pharmacokinetics

Metabolism / Metabolites 7-hydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene has known human metabolites that include 7,8,9,10-tetrahydrobenzo[a]pyren-7-yl hydrogen sulfate.

References

[1]. Glatt H, Pauly K, Frank H, Seidel A, Oesch F, Harvey RG, Werle-Schneider G. Substance-dependent sex differences in the activation of benzylic alcohols to mutagens by hepatic sulfotransferases of the rat. Carcinogenesis. 1994 Nov;15(11):2605-11. [2]. Surh YJ, Tannenbaum SR. Sulfotransferase-mediated activation of 7,8,9,10-tetrahydro-7-ol, 7,8-dihydrodiol, and 7,8,9,10-tetraol derivatives of benzo[a]pyrene. Chem Res Toxicol. 1995 Jul-Aug;8(5):693-8.

Solubility Data

Solubility (In Vitro)

DMSO: 250 mg/mL (917.97 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (7.64 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.08 mg/mL (7.64 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.6719 mL	18.3594 mL	36.7188 mL
	5 mM	0.7344 mL	3.6719 mL	7.3438 mL
	10 mM	0.3672 mL	1.8359 mL	3.6719 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.